The present invention relates to carbomethoxy methyl norbornanes having the generic formula: ##STR2## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; and one of R.sub.1 and R.sub.2 is methyl and the other of R.sub.1 and R.sub.2 is hydrogen, and to novel compositions using one or more of such norbornane derivatives to alter, modify or enhance the flavor and/or aroma of consumable materials or impart flavor and/or aroma to consumable materials.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) flavors and fragrances to (or in) various consumable materials. These substances are used to diminish the use of natural materials, some of which may be in short supply, and to provide more uniform properties in the finished product.
Application for U.S. Letters Patent, Ser. No. 133,870 filed on Mar. 25, 1980 relates to compounds generic to the compounds of the instant invention; carboalkoxy alkyl norbornanes having the generic formula: ##STR3## wherein the dashed line represents either a carbon-carbon single or a carbon-carbon double bond; R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen or methyl; with the proviso that one of R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is hydrogen; and with the further proviso that R.sub.3 and R.sub.4 are not both methyl, produced by the novel process of our invention and to novel compositions using one or more of such norbornane derivatives to alter, modify or enhance the flavor and/or aroma of consumable materials or impart flavor and/or aroma to consumable materials.
Mellor and Webb, J. Chem. Soc. Perkin Trans II, 1974 (I) 26-31 discloses production of the compounds having the structures: ##STR4## together with several other methyl substituted isomers thereof in admixture, according to the reaction: ##STR5## The Mellor and Webb article, however, does not disclose the reaction to take place at low temperatures in the presence of an alkyl aluminum halide or dialkyl aluminum halide whereby but two isomers are produced in a controlled fashion in high yields thus yielding an organoleptically acceptable mixture of carboalkoxy norbornane derivatives.